Stock Cooperative at 101 Chestnut Street, Boston MA 02108
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24 photos

$3,499,950

101 Chestnut Street, Boston MA 02108
Boston, MA 02108
Listed by Rebecca Davis Tulman and Leslie Singleton Adam
Bedrooms
2
Bathrooms
3
Living area
2,500 sqft
Year built
1918

About this home

Set within one of Beacon Hill’s most distinguished buildings, 101 Chestnut Street is celebrated for its gracious architecture, elegant courtyard and exceptional service. Unit E offers approximately 2,500 sq. ft. of expansive single-floor living with 2 bedrooms plus a library/office/guest room and 3 full baths. At the heart of the residence is an impressive 22' × 22' living and dining room, offering exceptional scale for both entertaining and everyday living. Desirable corner exposure brings natural light throughout, while the south-facing primary suite features generous proportions, an en suite bath and exceptional closet space. A separate guest wing provides wonderful privacy with a second bedroom, full bath and flexible library/office/guest room with an additional bath. Courtyard views, a well-appointed kitchen, concierge service, beautifully landscaped common roof deck and private storage complete this gracious Beacon Hill residence.

Highlights

Fireplace

Property details

MLS
MLS Property Information Network
MLS #
73576624
Property type
Stock Cooperative
Subdivision
N/A
Status
Active
Days on market
37
On market date
September 14, 2026
Stories
1
Total bathrooms
3
Garage spaces
N/A
Parking spaces
N/A
Lot size
N/A
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
Josiah Quincy
0.73 mi away · Grades -1-5
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
711
Student:teacher ratio
10.9:1
District
Boston
Middle
Cambridge Street Upper School
1.44 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
279
Student:teacher ratio
7.5:1
District
Cambridge
High
Snowden International School at Copley
0.51 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
485
Student:teacher ratio
12.8:1
District
Boston

Walkability

Blended score for Boston's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

92
Highly walkable
out of 100
EPA National Walkability Index
17.3 / 20 -- Most walkable
Google Places amenity density
100 / 100
Restaurants & cafes20
Grocery stores20
Parks20
Schools20
Transit stops20
Pharmacies20

Market position

How this listing compares to current activity in Boston, from live MLS data.

On the market 37 days -- 88 fewer days than Boston's current average of 125 days.
For reference, the median list price across 8,949 active listings in Boston right now is $85,000.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Est. monthly payment
$21,227/mo
$699,990 down
$2,799,960 loan
Principal & interest$18,160
Property tax (est.)$2,917
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated 20 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.